4.4 Article

A short and stereoselective synthesis of highly substituted cyclopropanes from α,β-unsaturated carbonyl compounds with dichloromethyl p-tolyl sulfoxide

Journal

TETRAHEDRON
Volume 64, Issue 22, Pages 5279-5284

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.03.034

Keywords

cyclopropane; highly substituted cyclopropane; dichloromethyl p-tolyl sulfoxide; alpha-sulfinyl carbanion; conjugate addition

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The reaction of the alpha-sulfinyl carbanion of dichloromethyl p-tolyl sulfoxide with a variety of alpha,beta-unsaturated carbonyl compounds gave highly substituted cyclopropanes (up to five substituents) in good to high yields with high stereoselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

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